Macrocarpine D

Details

• Internal ID: c0172cb4-7832-4030-b4a8-96ff8bc1e01a
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: [(1S,12S,13R,16S,17S,18R)-16,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methanol
• SMILES (Canonical): CC1C(C2CC3C4=C(CC(C2CO1)N3C)C5=CC=CC=C5N4)CO
• SMILES (Isomeric): C[C@H]1[C@@H]([C@@H]2C[C@H]3C4=C(C[C@@H]([C@@H]2CO1)N3C)C5=CC=CC=C5N4)CO
• InChI: InChI=1S/C20H26N2O2/c1-11-15(9-23)13-7-19-20-14(12-5-3-4-6-17(12)21-20)8-18(22(19)2)16(13)10-24-11/h3-6,11,13,15-16,18-19,21,23H,7-10H2,1-2H3/t11-,13-,15-,16+,18-,19-/m0/s1
• InChI Key: VTKMAZPMLOELMZ-WVMOBLFMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₂O₂
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.199428076 g/mol
• Topological Polar Surface Area (TPSA): 48.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9654	96.54%
Caco-2	+	0.8528	85.28%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4038	40.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8838	88.38%
OATP1B3 inhibitior	+	0.9396	93.96%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.5717	57.17%
P-glycoprotein inhibitior	-	0.8860	88.60%
P-glycoprotein substrate	+	0.6157	61.57%
CYP3A4 substrate	+	0.6442	64.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5791	57.91%
CYP3A4 inhibition	-	0.6529	65.29%
CYP2C9 inhibition	-	0.9190	91.90%
CYP2C19 inhibition	-	0.7231	72.31%
CYP2D6 inhibition	-	0.5936	59.36%
CYP1A2 inhibition	-	0.6338	63.38%
CYP2C8 inhibition	-	0.6838	68.38%
CYP inhibitory promiscuity	-	0.7598	75.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6346	63.46%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9929	99.29%
Skin irritation	-	0.7931	79.31%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7992	79.92%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.6591	65.91%
skin sensitisation	-	0.8791	87.91%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8904	89.04%
Acute Oral Toxicity (c)	III	0.5858	58.58%
Estrogen receptor binding	+	0.5546	55.46%
Androgen receptor binding	+	0.6285	62.85%
Thyroid receptor binding	-	0.5077	50.77%
Glucocorticoid receptor binding	-	0.6922	69.22%
Aromatase binding	-	0.5738	57.38%
PPAR gamma	-	0.7435	74.35%
Honey bee toxicity	-	0.8480	84.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.6598	65.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.40%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.64%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.47%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.40%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.69%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.47%	93.99%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.73%	88.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.46%	97.25%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.52%	100.00%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.10%	85.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.61%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.22%	94.45%

Plants that contains it

• Alstonia angustifolia

Cross-Links

• PubChem: 118715169
• LOTUS: LTS0042072
• wikiData: Q105292802